Synthesis of Heterocyclic Compounds from Imine and Study of Chromatography Applications.
Marwa T. Khattar1, Dr. Nagham M. Aljamali2*, Dr. Kasim K. Alasadi3
1M. Sc. Researcher, Chem. Dept., College of Education, Univ. of Kufa, Iraq.
2Assist. Prof., Chem. Dept., College of Education, Univ. of Kufa, Iraq.
3Assist. Prof., College of Science, Univ. of Kufa, Iraq
*Corresponding Author E-mail:dr.nagham_mj@yahoo.com
ABSTRACT:
The aim of this work, synthesis of heterocycles included more than one hetero atom like (N, S, O) to produce various cycles [3-8] membered ring. This work involved five parts, included synthesis of compounds [1-20] first part includes synthesis of three compounds [1,11,17] through reaction between 4-alimethyl amino benzaldehyde with different primary aromatic amines to give (schiff bases ), second part involved synthesis of compounds [2, 1218, 20] from reaction between schiff bases with (maliec anhydride m, cystiene, 3,5dinitro salcylic acid , 0-thiol benzoic acid, alanine ) to give (oxazepine, imidazolidine, oxazine ) third part synthesis of diazepine compounds [3-5] from reaction between oxazepine with (hydro guandine, thiosimecarbazide, thiourea ) four part involved synthesis of compounds [6-10] from reaction between Diazepine with (di chloro methane, benzoic acid, oxalic acid, di chloro ethane ) to give (three, four, five) rings, five part involved of compounds [13-16] from reaction between five membered with (phthalic anhydride, malic anhydride, oxalic acid, dichloro ethane) to give (three, five, six, eight), six part include: study of chromatography.
The structure of these compounds were characterized by (H.NMR, FI.IR, C.H.N) -techniques and their melting points, then study of chromatography behavior.
KEYWORDS: Oxazepine, diazepine, maziridine, schiff base, melamine, four membered, eight membered
Heterocyclic compounds used to develop of biological or medicinal interest to chemists (1). The compounds generally consist of (5,6,7-membered) saturated at unsaturated cycles of more than one hetero atom which may be similar or dissimilar(2). The aromatic-hetero cyclic polymers are one of versatile and widely utilized class of organic polymers, they are used in several applications(3) . oxazepine refers to any seven-membered ring containing au oxygen and nitrogen atom(4), synthesis of these compounds in this work is a class of pericyclic reaction which is classified as a (5+2=7), implying5-atom component plus 2- atom component leading to 7- membered cyring(5). Oxazepinederivative is used as an antibiotic, enzyme inhibitor, pharmacological interest (6) and have dical and biological important(7).
Chemical compounds built on a diazepines fold have recently emerged as potent inhibitors of theacetyllysine binding activity of bromodomain-containing proteins, which is required for gene transcriptional activation in cancer and inflammation(8). Diazepine derivatives are used as tranquilizers, anticonvulsant, anxiolytic, analgesics, sedatives, anti depressives and hypnotic agents. Diazepine continues. To be challenging end ever in synthetic organic chemistry(9) tetrazoles they are arowatic five membered ring containing four nitrogen atoms(10) Tetrazoles have been found to exhibit an exhibit antibacterial, antifungal, antihistamine and anti-inflammatory properties(11). Triazolesconntries an important class of organic compounds with divers agricultural, industrial and biological activities including, sedative, anti-convulsant-inflammatory(12), Literature survey reveals that 2-oxo-azetidines have shown various biological activities along with antimicrobial activity. In view of these findings some 2-oxo-azetidine derivatives of isoniazid have been synthesized and evaluated for anti-bacterial, antifungal and anti-tubercular activity (13). 4-oxo-azetidines are 4-membered cyclic amides derived from schiff bases which
contain B-lactam unit as an essential structure feature of its molecule (14). We have used schiff base condensation as the ring-closing step to synthesis oxazepine, diazepine, thio compound, the hetero atoms in there structure such as (S,N,O) explain variety of applications, antitumor, in the biological engineering and in other field of their specific structure(15). Schiff bases are anti-chemical good for some types of bacteria and fungi (16). Schiff base posses antituberior and anticancer activity(17) Gas chromatography (c-c) analysis of basic organic compounds (e.g. amines, basic drugs and azo dyes)is a challenge to the analyst, especially when the compounds are at low concentration(18) and these parathion mechanism depend on the selective phase, rate of carrier gas, temperature column(19) this technique is used to separate the numerous compounds, particularly organic compounds such as alcoholsand hydrocarbons aolastarate ketones and, Aldehyde etc(20)
Experimental Apparatus:-
All chemicals used (purity 99.98%), FT.IR-spectra: were recorded on Shimadzu 8300, KBr-disc, HNMR-spectra were recorded on Varian 300 MHZ spectrometer using TMS as an internal standard and elemental analysis (C.H.N)-elemental (Analyses system GmbH)-measurements were made at Department of Chemistry, Kashan University. Iran. The melting points were determined in open capillary tubes by electro thermal 9300 LTD, U.K.
Synthesis of Compounds [1,2]
A mixture of 4- nitro aniline (0,0 1mole) and 4-dimethyl amino benzaldehyde (0,01 mole) in the presence of absolute ethanol with drops of glacial acetic acid and reflux for (2h), the precipitate was filtered and dried with recrystallized to yield (86%) of compound [I], which (0.01mole) reacted with (0.01mole) of maleic anhydride respectively in presence of dry benzene with refluxing for(4h), the precipitates filtered, recrystallized from ethanol to produce(88%) of compound[2].
Synthesis of Compounds[3-5]
A mixture of(0.01mole) of compound [2] with(o.o1mole) of one of(hydro guandine, thiosemicarbazide, thiourea) were refluxed in presence of dry benzene for (4h), the precipitates filtered, recystallized from dry benzene to produce(80,82 and 180)% of compound[3],compound[4] and compound[5], respectively.
Synthesis of Compounds[6,7]
A mixture of (0,001 mole) of (dichloromethyl ) in the presence of KOH in absolute ethanol with drops of glacial acetic and reflux for (42h), (0,001 mole) of (benzoic acid) in the presence of (4N) hydro chloric acid and reflux for (36h), the precipitate was filtered and dried with recrystallized to yield(81,85)% of compound[6], compound[7], respectively.
Synthesis of Compound[8]
The reaction of compound[5] (0.01 mole) with (dichloro ethane) (0.01 mole) in the presence of KOH in absolute ethanol for (3h), resulted in the formation (82%) of compound [8]
Synthesis of Compounds[9-10]
Ethanolic mixture of(0.01 mole) of compound[4] with(0.01 mole) of oxalic acid and (0.001mole) of dichloro methane to were refluxed for (4h) yield(84,85)% of compound[9] and compound[10] respectively.
Synthesis of Compounds[11-14]
A mixture of (0.01 mole) of melamine with (o.o1 mole) of 4-dimethyl benzaldehyde in the presence of absolute ethanol with drops of glacial acetic acid and reflux for (4h), the precipitate was filtered and dried with recrystallised to yield (83%) of compound[11] which(0.01 mole) with (0.01 mole) of cystein respectively in presence of dry benzene with refluxing for (7h) the precipitate was filtered and dried with recrystallized to yield (80%) of compound[12], which (0.001 mole) with one of (0.001 mole) of (phthalic an hydride) in the presence of acetone with reflux for (4h) (0.003 mole) of (maliec acid) in the presence of absolute ethanol with droups of glacial acetic acid with reflux for(7h), The precipitates filtered, recrystallized to give (80,80) % of compound[13], compound[14] respectively.
Synthesis of Compounds[15,16]
(1 mole) of compound [13] with (2mole) of one of (oxalic acid, dichlorechane) were refluxed in presence of Ethanol and presence of K2CO3 for (7-8h), the precipitate was filtered and dried with recrystallized resulted in the formation (80,80)% of compound[15], compound[16] respectively.
Synthesis of Compounds[17-20]
A mixture of(0.03 mole) of 4-dimethylaminopemzaldehyd, with(0.01 mole) of melamine in the presence of absolute ethanol with drops of glacial acetic acid and reflux for (4h), the precipitate was filtered and dried with recrystallized to yield(82%) of compound [17], which of one (0.03 mole) of (3,5-dinitrosakylicacid, (0.004 mole) of o-thiol benzoic acid and alanine) were refluxed in presence of dry benzene for (9h), the precipitate was filtered and dried with recrystallized to yield (80,82,80)% of compound [18], compound[19] and compound[20], respectively.
Scheme (1):Preparation of compounds [1-10]
Scheme (2):Preparation of compounds [11-20]
Analysis of Compounds [2, 3, 4, 5, 9 and Mixture] by Gas Chromatography:
Preparation of diluted solutions (( concentration of 1ppm for vehicles)) of compounds [2, 3, 4, 5,9 and Mixture] after dissolved with ethanol was also attended by a mixture of compounds which prepared by mixing 10ml of each solution individually after shaking continuous., injected models by using a syringe(Hamilton) with a capacity of 10ml individually and then injected the mixture, and then install the measurement conditions through the use of nitrogen a gas flow of 25ml/min bus speeds and injection temperature was 25Cº degrees higher than the temperature separation column and then use a flame ionization detector is 50Cº higher than the temperatures of the column either column temperature programmed gradual increase of (90-160)Cº, taking into consideration the maximum temperature to avoid damage to the column. All data are shown in Table (1) and figures (11-16).
RESULTS AND DISCUSSION:
All synthesized compounds [1-20] were characterized by FT. IR- spectra, (C.H.N)- analysis, melting points and some of them by H.NMR-spectra]. FT.IR-spectra showed appearance absorption bends at (1604) cm-1 due to (CH=N) imine group, absorption band at (1350) cm-1 due to (C-NO2) nitro group, absorption bends at (1298)cm-1 due to (-N(CH3)2) dimethyl amine in compound [A1]. Appearance of absorption band at (1689)cm-1 due to carbonyl group (CO) lactam (CO-N), absorption band at (1714)cm-1 due to carbonyl group (CO) of lactone (CO-O), absorption band at (2968)cm-1 due to (C-H) aliphatic, absorption band at (1408, 1284)cm-1 due to (C-NO2) nitro group and (N(CH3)2) in compound [A2]. Appearance of absorption band at (1691, 1691, 1698)cm-1 due to (CO-N) lactam, absorption band at (3367, 3425, 3201, 3294, 3333, 3419)cm-1 due to NH2, absorption band at (3041, 3100, 3030)cm-1 due to (CH=CH) alkene, absorption band at (2929, 2933, 2999)cm-1 due to (C-H) aliphatic, absorption band at (1284, 1250, 1298)cm-1 due to (N(CH3)2) in compounds [A3, A4, A5], absorption band at (1390, 1346)cm-1 due to (C-NO2) nitro group in compounds [A3, A5], absorption band at (815)cm-1 due to (C=S) in compound [A5]. Appearance of absorption band at (1680, 1689)cm-1 due to (CO-N) of lactam, absorption band at (1608, 1606)cm-1 due to (C=N) indo cycle of lactam, absorption band at (2910, 2929)cm-1 due to (C-O) aliphatic, absorption band at (1355, 1384)cm-1 due to (C-NO2), absorption band at (1230, 1250)cm-1 due to (N(CH3)2), absorption band at (3030, 3061)cm-1 due to(CH=CH), in compound [A, A7], absorption band at (3282) cm-1 due to (NH) in compound [A6]. Appearance of absorption band at (1699)cm-1 due to (CO-N) of lactam, absorption band at (3009)cm-1 due to (CH=CH) of alkene, absorption band at (2897)cm-1 due to (C-H) aliphatic, absorption band at (1380)cm-1 due to (C-NO2) nitro group, absorption band (1280)cm-1 due to (N(CH3)2), absorption band at (798)cm-1 due to (C=S) in compound [A8]. Appearance of absorption band at (1672, 1689)cm-1 due to (CO-N)of amide, absorption band at (3304, 3321)cm-1 due to (NH) of amide, absorption band at (3059, 3089)cm-1 due to (CH=CH) of alkene, absorption band at (1220, 1284)cm-1 due (N(CH3)2) in compounds [A9, A10]. Appearance of absorption band at (1618)cm-1 due to (-CH=N-) of imine group, absorption band at (1608)cm-1 due to (C=N) of indo cycle of melamine, absorption band at (3435,(3435, 3421))cm-1 due to (NH2) of amine, absorption band at (1240)cm-1 due to (N(CH3)2) in compound [A11], which disappeared and other bands are appear at (1670)cm-1 due to (CO-N) of amide and two bands at (1598, 2362)cm-1 due to (C=N) of indo cycle of melamine, (SH) and band at (2972)cm-1 due to (C-H) aliphatic, absorption band at (3230, 3365)cm-1 due to (NH2) and band at (2286)cm-1 in compound [A12]. Appearance of absorption band at (1695, 1664)cm-1 due to (CO-N) of amide, absorption band at (1600)cm-1 due to (C=N) of indo cycle of melamine, absorption band at (2960, 2922)cm-1 due to (C-H) aliphatic, absorption band at (1246, 1240)cm-1 due to (N(CH3)2) in compounds [A13, A14] and band at (2362)cm-1 due to (SH) and band at (3340, 3281)cm-1 due to (NH2) in compound [A13] and band at (1365)cm-1 due to (CH2-S) in compound [A14]. Appearance of absorption band at (1681, 1684)cm-1 due to (CO-N) of lactam , absorption band at (1604)cm-1 due to (C=N) indo cycle of melamine and bands at (2939, 2904)cm-1 due to (C-H) aliphatic and bands at (1398, 1320)cm-1 due to (CH2-S) and bands at (1298, 1294)cm-1 due to (N(CH3)2) in compounds [A15, A16]. Appearance of absorption bands at (1624, 1588, 1298)cm-1 due to (CH=N) of imine group, (C=N) of indo cycle of melamine and (N(CH3)2) respectively in compound [A17]. Appearance of absorption band at (1688, 1680, 1662)cm-1 due to (CO-N) of amide absorption band at (1595, 1608, 1597)cm-1 due to (C=N) of indo cycle of melamine and bands at (1255, 1230, 1234)cm-1 due to (N(CH3)2) in compounds [A18, A19, A20], absorption band at (1431)cm-1 due to (CH-S) in compound [A19], absorption bands at (2904, 1371, 1165)cm-1 due to (CH) aliphatic, (C-NO2) and (C-O-C) ether group in compound [A18]. Absorption band at (2908, 3230)cm-1 due to (C-H) aliphatic and (NH) amine group in compound [20]., all data are shown in Table (2) and figures (1-5).
Table (1). Specification Used Capillary Columns
|
Polarity |
Max operatory Temp.(M.O.T) |
Column dimension |
Formula |
Composition |
Liquid phase |
|
Low polar |
(300) |
0.25mm I.D 0.12 Mm d.f |
|
2,3-di-o-propionyl-6-t-butylsilyl derivative of ᵞ-cyclodextrin phase |
DP5-25 |
|
Moderately polar |
-20C؛-280C؛-(300)C؛ |
0.25mm I.D 0.25Mm d. f |
|
14%Cyanopropyl phenyl poly siloxane |
FS-BP10 |
1H.NMR-Spectrum:
H.NMR-Spectrum of compounds showed signal at δ(8.66) for one proton of azomethine group (-CH=N-) , sign at and (2.99) for protons of dimethyl amine (N(CH3)2), two signal at and (6.74-7.66) for protons of phenyl rings in compound [A1]. Signal at (9.63) for proton of (O-CH-N) of oxazepine ring, signal at (6.06) proton of (CO-CH=CH-CO) of alkene in oxazepine ring, signal at and (2.85) for protons of (N(CH3)2), two signal at and (6.74-7.66)protons of phenyl rings in compound [A2]. Signal at and (2.99) protons of (N(CH3)2), signal at and (2.47) of proton of diazepine ring, doublet signal and (2.25) protons of alkene (CO-CH=CH-CO), two signal at and (6.74- 7.65) for protons of phenyl rings, signal at and (9.63/ 0.42)for protons of amide (-NH-CO-NH2) in compound [A4]. Signal at (2.46) proton of (N-CH-N) in diazepine ring, signal at and (4.54) proton of (NH2-CS-), signal and (2.98) proton of N(CH3)2 , two signal at and (6.71, 6.73) protons of alkene in diazepine ring (-CO-CH=CH-CO-), two signal at and (6.88 -7.65) for protons of phenyl rings in compound [A5] signal at and (2.95) proton of (N-CH-N) in diazepine ring, two signal at and (6.52 -7.67) protons of phenyl rings, two signal at and (6.02, 6.09) protons of alkene (CO-CH=CH-CO)in diazepine ring, signal at and (2.54) for protons of N(CH3)2 , signal at and (3.83) proton of amine (-NH-) in four membered cycle , at and (3.01) protons of methylene in (-C=N-CH2-NH) in four membered cycle in compound [A6]. Signal at and (3.39) of (N-CH-N) proton of diazepine ring, signal at and (2.47) protons of N(CH3)2 , two signal at (1.82, 2.06) for triblete of (CH2- N) of azirine cycle, two signal at (6.06, 6.18) of doublet signal (CO-CH=CH-CO) alkene in diazepine ring, two signal at (6.53, 7.94) of protons of phenyl ring(20 ,21) in compound [A8]. Signal at (SH) thiol group, signal at (3.39) proton of (NH) amine at and (2.47)proton of N(CH3)2 , signal at (2.06) proton of (N-CH-N), three signal and (1.82 , 1.74 , 1.37)proton of (-CH-CH2-) , two signal at (6.53, 7.65) protons of phenyl rings in compound [A13]. Signal at (2.35) proton of N(CH3)2 , two signal at and (2.48, 2.54) for protons of (CO-CH2-CH2-CO) of cycles, threesignal at (3.01, 2.95 , 2.85) for protons of (N-CH-CH2-S) of eight membered ring , two signal at (6.52, 7.67) for protons of phenyl ring in compound [A14]. Signal at (3.01)proton of (N-CH-N) of imidazol one ring , two signal at and (3.38 , 3.01) for protons (N-CH-CH2-S) of thiazine ring , signal at (2.48) for proton of N(CH3)2, two signal at (6.74, 7.67) for protons of phenyl rings in compound [A15]. Signal at (8.66) proton of imine group (CH=N)(20 ,21) , two signal at (6.74, 7.66) protons of phenyl rings, signal at (2.99) protons of N(CH3)2in compound [A17], all data are shown in Table (3) and figures (6-10).
(C.H.N)-Analysis:
(C.H.N)- Analysis, from compared the calculated with found data of these compounds, the results were comparable, the data of analysis, MF, names and melting points are listed in table (4).
Table (2) .FT.LR-data(cm-1) of compounds[1-20].
|
Others |
(-CO-O-) of Lactone |
(-CO-N-) of Lactam |
(C=N) Imine group |
Comp. No. |
|
ـــــــــــــــــــــــــــــ |
ــــــــــــ |
ــــــــــــ |
1604 |
[1] |
|
(C-NO2):1458 ,(N(CH3)2): 1284, (C-H aliphatic): 29,8 |
1714 |
1689 |
ـــــــــــ |
[2] |
|
(C-NO2): 13%, (N(CH3)2): 1284, (C-H aliphatic): 2929, (CH=CH): 3041, (NH2): 3425, 3367 |
ــــــــــــ |
1691 |
ـــــــــــ |
[3] |
|
(N(CH3)2):1250, (CH=CH): 3100, (C-H aliphatic): 2933, (NH2): 3201, 3294 |
ــــــــــــ |
1691 |
ـــــــــــ |
[4] |
|
(C-NO2): 1346, (N(CH3)2): 1298, (C-H aliphatic): 2999, (CH=CH): 3030, (NH2):3333, 3419, (C=S): 815 |
ــــــــــــ |
1698 |
ـــــــــــ |
[5] |
|
(C-NO2):1355, (N(CH3)2): 1230, (C-H aliphatic): 2910, (CH=CH): 3030, (NH): 3282, (C=N) indo cycle of diazitedine Four membering |
ــــــــــــ |
1680 |
ـــــــــــ |
[6] |
|
(C-NO2): 1384, (N(CH3)2): 1250,(C-H aliphatic): 2929, (CH=CH): 3061, ((C=N) of ando cycle of Four membring): 1606 |
ــــــــــــ |
1689 |
ـــــــــــ |
[7] |
|
(C-NO2): 1380, (N(CH3)2): 1280,(C-H aliphatic): 2897, (CH=CH): 3009, (C=S): 798 |
ــــــــــــ |
1699 |
ـــــــــــ |
[8] |
|
(C-NO2): 1356 (N(CH3)2): 1225, (CH=CH): 3059, ( (NH) of amide):3304 |
ــــــــــــ |
1672 |
ـــــــــــ |
[9] |
|
(N(CH3)2): 1284, (CH=CH): 3089,(C-H aliphatic): 2968, (NH of amide)=3321 |
ــــــــــــ |
1689 |
ـــــــــــ |
[10] |
|
(N(CG3)2): 1240, (NH2): 3435,3421, ( (C=N)of indo cycle of melamine)=1588 |
ــــــــــــ |
|
1618 |
[11] |
|
(N(CH3)2): 2286, (SH): 2362, (C-H aliphatic): 2972, (NH2): 3230, 3365, (C=N) in docycl of melamine |
ــــــــــــ |
1675 |
ـــــــــــ |
[12] |
|
(N(CH3)2): 1246, (SH): 2362, (CH aliphatic): 2960, (NH2): 3340, 3281, ( (C=N) of indo cycle of melamine): 1600 |
ــــــــــــ |
1695 |
ـــــــــــ |
[13] |
|
(N(CH3)2): 1240, (CH2-S): 1365, (C-H aliphatic): 2939, ( (C=N) indo cycle of melamine):1604 |
ــــــــــــ |
1664 |
ـــــــــــ |
[14] |
|
(N(CH3)2): 1298, (CH2-S): 1398, (C-H aliphatic): 2939(C=N) indo cycle of melamine |
ــــــــــــ |
1681 |
ـــــــــــ |
[15] |
|
(N(CH3)2): 1294, (CH2-S): 1320, (C-H aliphatic): 2904(C=N) indo cycle of melamine |
ــــــــــــ |
1684 |
ـــــــــــ |
[16] |
|
(N(CH3)2): 1298, (C=N) of indo cycle of melamine |
ــــــــــــ |
ــــــــــــ |
1624 |
[17] |
|
(C+NO2): 1371, (N(CH3)2)=1255, (C-H aliphatic): 2904( (C=N) indo cycle of melamine): 1595, (C-O-C): 11, 5 |
ــــــــــــ |
1688 |
ـــــــــــ |
[18] |
|
(N(CH3)2): 1230, (CH-S): 1431, ( (C=N) of indo cycle of melamine): 1608 |
ــــــــــــ |
1680 |
ـــــــــــ |
[19] |
|
(N-(CH3)2): 1234, (NH): 3230, (C-H aliphatic): 2908( (C=N) indo cycle of melamine): 1597 |
ــــــــــــ |
1662 |
ـــــــــــ |
[20] |
Table( 3 ). H.NMR(.ɓ. ppm) of Some Compounds.
|
Other peaks |
N(CH3)2 |
(N-CH-N) of alkene |
(CO-CH=CH-CO) of alkene |
Comp No. |
|
(8,66) proton of(Iminegroup) (6,74-7,66) proton of phenyl rings |
(2,99) |
ـــــــــ |
ــــــــــ |
[1] |
|
(9,63) proton of oxazepine ring (O-CH-N), (6,74-7,66) proton of phenyl rings. |
(2,85) |
ـــــــــ |
(6,06) in oxazepine ring |
[2] |
|
(4,54)proton of (NH2-CS-), (6.88-7.65) proton of phenyl rings. |
(2,98) |
(2,46) |
(6,71,6,73) in diazepine ring |
[5] |
|
(1.82, 2.06) proton of (CH2-N) of azirine cycle, (6,53,7.94) protons of phenyl rings. |
(2,47) |
(3,39) |
(6,06,6,18) in diazepine ring |
[8] |
|
(9.63,10.42) protons of amide (-NH-CO-NH2), (6.74-7.65) protons of phenyl ring. |
(2,99) |
(2,47) |
(2,25) in diazepine ring |
[4] |
|
(3.83) proton of amine(-NH-), (3.51) of (6.52-7.67) of phenyl rings. |
(2,54) |
(2,95) |
(6,02,6,09) in diazepine |
[6] |
|
(5.91) of thiol group (SH), (3.39) of amine (NH), (1.82,1.74,1.37) of (CH-CH2), (6.53-7.65) phenyl rings. |
(2,47) |
(2,56) |
ــــــــــ |
[13] |
|
(2.48,2.54) proton of (CO-CH2-CH2-CO), (6.52-7.67) proton of phenyl rings. |
(2,35) |
(3,88) |
ــــــــــ |
[14] |
|
(3.38,3.51) proton of (N-CH-CH2-S), (3.51) proton of imidazolone (N-CH-N), (6.74-7.67) proton of phenyl rings. |
(2,48) |
ـــــــــ |
ــــــــــ |
[15] |
|
(8.66) proton of Iimine group, (6.74-7.66) proton of phenyl rings. |
(2,99) |
ـــــــــ |
ــــــــــ |
[17] |
Table (4). Physical properties and (C.H.N) analysis of compounds [1-20]
|
Found |
M.P Co |
M.F |
Comp. No. |
||
|
N % |
H % |
C % |
|||
|
15.113 |
5.268 |
66.120 |
159 |
C15H15N3O2 |
[1] |
|
11.209 |
4.398 |
62.005 |
180 |
C19H17N3O5 |
[2] |
|
20.349 |
4.651 |
58.574 |
208 |
C20H20N6O4 |
[3] |
|
19.432 |
4.401 |
56.383 |
198 |
C20H20N6O5 |
[4] |
|
16.156 |
4.313 |
56.154 |
204 |
C20H19N5O4S |
[5] |
|
19.795 |
4.582 |
59.813 |
206 |
C21H20N6O4 |
[6] |
|
16.843 |
4.274 |
65.315 |
214 |
C27H22N6O4 |
[7] |
|
15.291 |
4.294 |
58.265 |
182 |
C22H21N5O4S |
[8] |
|
17.314 |
3.603 |
55.105 |
234 |
C22H18N6O7 |
[9] |
|
19.114 |
4.371 |
57.482 |
202 |
C21H20N6O5 |
[10] |
|
38.011 |
5.246 |
55.558 |
359 |
C12H15N7 |
[11] |
|
31.102 |
5.075 |
50.009 |
>360 |
C15H19N8OS |
[12] |
|
22.624 |
4.315 |
56.153 |
>360 |
C23H22N8O3S |
[13] |
|
18.342 |
4.126 |
53.303 |
260 |
C27H26N8O7S |
[14] |
|
18.482 |
29.917 |
54.016 |
222 |
C27H18N8O7S |
[15] |
|
20.416 |
4.574 |
59.518 |
240 |
C27H26N8O3S |
[16] |
|
24.020 |
6.068 |
69.121 |
>360 |
C30H33N9 |
[17] |
|
18.115 |
3.147 |
35.086 |
>360 |
C51H39N15O18 |
[18] |
|
13.352 |
4.593 |
65.891 |
>360 |
C51H45N9O3S3 |
[19] |
|
22.887 |
6.106 |
64.071 |
>360 |
C39H45N12O3 |
[20] |
Fig (1) .FT.IR- Spectra of compound [4 ]
Fig (2) .FT.IR- Spectra of compound [8 ]
Fig (3) .FT.IR- Spectra of compound [ 11 ]
Fig (4) .FT.IR- Spectra of compound [ 12 ]
Fig (5) .FT.IR- Spectra of compound [ 17 ]
Fig (6) .1H.NMR- Spectra of compound [ 2 ]
Fig (7) .1H.NMR- Spectra of compound [ 10 ]
Fig (8) .1H.NMR- Spectra of compound [ 12 ]
Fig (9) .1H.NMR- Spectra of compound [ 13 ]
Fig (10) .1H.NMR- Spectra of compound [ 19 ]
Fig(11): Chromatogram of comp.[2]
Fig(12): Chromatogram of comp.[9]
Fig(13): Chromatogram of Mixture[2-5 ,9]
Fig(14): Chromatogram of comp.[5]
Fig(15): Chromatogram of comp.[4]
Fig(16): Chromatogram of comp.[3]
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Received on 05.07.2014 Modified on 20.07.2014
Accepted on 10.08.2014 © AJRC All right reserved
Asian J. Research Chem. 7(8): August 2014; Page 734-747